Ethanol → 7-ethoxy-N-(3-ethynylphenyl)-6-nitroquinazolin-4-amine

HRID 1051119Notes

Reaction equation

HRID 1051119 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16](F)=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2].[CH2:24]([OH:26])[CH3:25]>>[CH2:24]([O:26][C:16]1[CH:15]=[C:14]2[C:19]([C:10]([NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[CH:2])[CH:4]=3)=[N:11][CH:12]=[N:13]2)=[CH:18][C:17]=1[N+:20]([O-:22])=[O:21])[CH3:25]

Participants

3

Reactant 2

HCID 702EthanolHCID 59142759N-(3-ethynylphenyl)-7-fluoro-6-nitroquinazolin-4-amine

Product 1

HCID 867303767-ethoxy-N-(3-ethynylphenyl)-6-nitroquinazolin-4-amineYield 93.4%

Conditions

Temperature
80 °C

Procedure

Na (1.4 g, 0.060 mol) was carefully dissolved in 80 ml of anhydrous ethanol to form a clear solution, then N-(3-ethynylphenyl)-7-fluoro-6-nitroquinazolin-4-amine (8 g, 0.025 mol) was added and stirred for 4 hours at 80° C. The solution was concentrated under reduced pressure to remove excess ethanol, and 50 ml H2O was added. The resulting solid precipitate was filtered and dried under vacuum to get 7-ethoxy-N-(3-ethynylphenyl)-6-nitroquinazolin-4-amine as yellow solid 8.1 g (93.4% yield).

Workup

  1. customto form a clear solution
  2. concentrationThe solution was concentrated under reduced pressure
  3. customto remove excess ethanol, and 50 ml H2O
  4. additionwas added
  5. filtrationThe resulting solid precipitate was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-ceb948152e1444e1b1337ab358f0337b
Source dataset
uspto-grants-2016_07
Patent number
US09388160B2

Reaction notes

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